Just One Last Time
by KittenOfDoomage
Summary: Based on a Tumblr gif that broke my feels. AU After Sam falls into the cage, Dean asks Cas for one more favour.


**So this is a little oneshot based off of a gif on Tumblr that has literally been keeping me awake at night. So I had to write it, in between chapters of Unto My Grace. I'm probably going to break my own feels here.**

**Set after Sam has fallen into the cage with Lucifer and Michael, so possible spoilers up to Season Five.**

**Summary: After Sam falls into the cage, Dean asks Cas for one more favour. On Dean's days off, he visits Sam in different time periods, even if only for an hour or two. Sam never tells Dean about these visits.**

* * *

Dean sat on the hood of the Impala, staring up at the sky. The beer in his hand had long since gotten warm, and he didn't feel like drinking it. One beer would lead to another, and another, and maybe he wouldn't have the guts to ask what he was going to. He _needed_ this. The past few weeks with Lisa and Ben had helped to a degree, but what he really need, all he'd ever needed, was his baby brother.

But Sam was gone.

Sam was in the pit, and he'd made Dean promise to go live the apple pie life he'd always wanted. And maybe once upon a time, he had wanted that. Maybe he'd dreamt of the white picket fence, two point four kids and dog napping on the lawn.

Only now, all he dreamt about was his brother, his lost family, the fact that he was in actual fact, _completely alone._

So he had to ask, had to try.

'Cas?' He asked the empty air around him. 'I need you.' His voice was broken and pleading. He sounded pitiful even to his own ears. 'Please...'

A fluttering of wings, and when Dean looked to his right, Castiel stood before him, an undistinguishable look on his face. 'Dean?'

'Cas.' The last remaining Winchester slid from the bonnet of the car, standing as straight as he could. He threw the beer off to the side; he wasn't going to drink it anyway. 'I need to ask you something.'

The angel nodded, a slight frown on his face as if he knew what Dean was thinking.

'I need to see Sam again. You said that time was fluid...' Dean took a breath. 'Can I go back? Just to see him. To see my baby brother?'

Castiel's mouth set into a thin line. 'You cannot change what has happened Dean. You know this.'

'I know, I know. And I'm not gonna try. I just...just need...' He didn't even know how to form into words what he needed. He was living the life Sam wanted for him. He was doing the regular job, the regular family thing, barbecues, bars - he should have been happy. Except he _couldn't _be. 'Please...I'm begging you here, please.'

'Dean, I think that's a bad idea...'

'It probably is. But since when have we had _good_ ideas? Look, I won't tell him anything. Not about the angels or Lucifer or any of that. I just...I just need to see him, Cas.' Dean was outright pleading now, and Cas softened a little.

'Okay.' He nodded, relenting. Dean blinked, obviously thinking he would need more persuading. 'I can give you some time to see your brother. But you cannot tell him anything. Nothing about the battles you will face. You can choose the time you go to.' He looked around. 'This seems like a safe place.'

Dean stepped forward. 'Thank you.'

'You have two hours.' Cas said quietly. 'Then I will pull you back. When would you like to go to?'

The former hunter thought for a moment, smiling as a memory came over him. 'When Sam was eight, Dad went on a hunting trip without us. I was watching him, and we went to the park to play football. Sam cut up his knee real bad, but he was so happy to be a real kid for a while. I'd like to see him then.' _Before everything started to destroy us._

Cas nodded. 'Focus on that time. I will rely on it to guide you.' He raised two fingers towards Dean, and placed them on his forehead.

Night turned to day in an instant, and Dean opened his eyes to green. The light was blinding for a second, and then he was stood in a park, surrounded by trees and bushes. Children's playful cries came from behind him, and he turned, seeing a playground full of kids running around. To the left, an open field, and he saw himself, younger, throwing a pigskin to a smaller boy.

_Sammy_.

His heart beat a little harder in that moment as he took them in. By that age, Dean was already hardened around the edges, desperate to protect his brother. The amulet was already around his neck, and he remembered that he'd dumped it. He wished so bad that he hadn't now. Sam had given that to him, and he'd thrown it when the going got rough. His hand came up to his unadorned neck and he choked down the urge to cry.

He watched for long moments as the younger versions of Dean and Sam played football, laughing and giggling as they threw the ball to each other, tackled each other and were generally _children. _John Winchester had never encouraged this kind of play. He let Sam play soccer at school once, and he'd won a trophy, but he'd never encouraged the hobby. The only hint they had that he was proud was the fact that the trophy sat gathering dust in a storage locker.

Little Dean wandered off for a moment, distracted by a pretty girl. Even at age twelve, he'd had an eye for the ladies, and a charm to match no other. Little Sam watched, then ran to the jungle gym, taking advantage of his brother's distraction. But Dean remembered this, remembered that he'd known where Sammy was the whole time. He never let his brother out of his sight.

Dean walked towards the park and sat on the bench, just watching his little brother play. It was getting darker now, and Dean knew he didn't have long left. He wished he could talk to Sam, but knew his younger self would be on guard straight away. Kids filtered out of the playground, and Sammy wasn't paying attention. He slipped, catching his knee on the wooden bar at the bottom of the jungle gym. Like a shot, Dean was up, before the boy could even let out a single cry.

'Hey, hey, kiddo.' He bent down in front of the eight year old version of his younger brother and smiled gently. 'It's not bad.'

'I'm okay.' Sammy insisted. 'I won't cry.' But Dean could see those big old fat tears threatening. John Winchester hadn't quite gotten it into Sam yet that he wasn't _supposed_ to cry, because hunters were strong and brave, and these little injuries didn't get to them. Except John had cried. A lot. Only he thought Dean didn't know.

'You alone out here?' Dean asked, knowing that any minute now, and angry twelve year old would be in his face.

'No. My big brother is over there.' Sam pointed and Dean looked, but couldn't see himself. Then he remembered why this date stuck so prominently in his mind. He'd gone off with some girl who'd given him his first kiss, and he'd only been gone for ten minutes, but he'd come back and Sammy had been hurt. The little boy frowned. 'Oh. He'll be back soon.'

'It's okay, I'll stay with you.'

Sammy nodded, then squinted up at him. 'You look like someone I know.' He said. 'You look a little like my dad.'

'Do I?'

'Maybe.'

Dean chuckled. 'You're a brave little guy huh?'

'My dad doesn't think so. Dean always has to protect me. Dad says it all the time. "Watch out for Sammy, look after your brother". I'm big enough to look after myself!' He sounded pretty angry, and Dean smiled a little. 'And I try to be brave, cos there's no one to protect Dean, ya know?'

'Protect Dean from what?'

'What my dad hunts.' He paled a little then. 'Well, from the monsters.'

'Monsters?' Dean enquired innocently. Sammy looked up at him with suspicion.

'You're a hunter.' He stated, and Dean blinked. Was he that obvious? 'You talk like Uncle Bobby. And you smell kinda like him and Dad. Whiskey and engine oil.'_  
_

Dean laughed out loud at that. 'Yeah, I'm a hunter. And I know you're Sammy Winchester.'

Sam puffed his chest out a little, proud. 'I am. And Dean's my big brother.'

'I know.' Dean said fondly.

'You kinda look like Dean, actually.' Sam pondered. 'But you couldn't _be_ Dean, cos that would be silly.'

'SAMMY!' The yell was urgent, and Dean knew his time was up as a tug started in his stomach. 'SAMMY!' Little Dean was pounding towards them across the field.

'I gotta go, kiddo. See you around, yeah?'

'Bye!' Sam waved as Dean slipped off before his younger self came over. As he hid himself in the trees, watching himself fuss over the cut Sammy had obtained whilst playing, Castiel pulled him back.

Sammy moaned that he was fine and there was no need to tell Dad. He glanced once in the direction the man he'd been speaking to had gone.

He never told his big brother what had happened that day.

* * *

Dean gasped, waking up from his nightmare with a shock. He groaned and ran a hand down his face, seeing that it was only ten minutes until Lisa's alarm went off and he needed to get Ben up for school. He'd been living with them for four months now, and was settled into the routine. Today was his day off, and on his day off, Ben was his responsibility to get ready for school.

He climbed out of bed and padded down to the bathroom, getting the usual morning issues done first. Then he headed to the kitchen and switch the coffee machine on, before pulling out everything that was required for breakfast and Ben's school lunch.

Two hours later, he sat in the house, contemplating the bottle of whiskey stashed in the kitchen cupboard. It was ten in the morning, and he was fairly certain that a fifth of whiskey at this hour would qualify as alcoholism. He'd tried so hard to cut back for Lisa and Ben, but sometimes it was the only way he could sleep.

He was antsy and thinking too much again. And thinking too much took his feet to the garage, keys to the Impala in hand. He never used her anymore. He used the beaten up old truck, the _normal_ vehicle he'd acquired for his _normal_ life. _Damn you Sam, damn you for this stupid promise when I should be out looking for a way to drag you back topside.__  
_

Within an hour he was back out in the deserted field he'd been sat in three months before, calling out for Cas. It took a few minutes, but the angel arrived, a look on his face that told him he knew exactly what Dean wanted.

'Your previous visit did not sate your need for your brother's company?'

'You know it didn't.' Dean muttered. 'Come on Cas. Just two hours. Like last time.'

'Did you want to go to the same time?'

'No.' The former hunter shook his head. 'No. I know where I want to go this time.' Castiel sighed and then nodded.

'Very well.'

* * *

When Dean opened his eyes this time, he was stood in a parking lot of a motel called the "Sunningdale Arms". He didn't remember the name, but he did remember the Impala being parked outside. Dad had taken him for some shooting practice in the woods because Sammy was sick. So they'd left him alone for most of the night.

He moved over to the motel doors, looking for the number. He didn't quite remember the door number, but when he peered in through the windows, it didn't take long to sift through the extra-marital affairs and business meetings to find the boy sat at a table with a book opened and his head buried in it. He smiled, looking at ten year old Sammy, already heavy into the booksmarts.

Raising a hand, he rapped at the door with his index finger. Sam took a long time to answer the door, but when he did, he held a small pistol and it was aimed at Dean's chest.

'Whoa, kiddo. Not gonna hurt you.'

Sam's eyes widened as he recognised the man at the door. 'You're...you're the hunter from the park.'

'You remember me?' Dean asked, warily.

'Yeah, when I cut my knee.' He looked around. 'Is there a problem? Should I call my dad?'

'No...no...actually I came to see you?'

Sam narrowed his eyes a little. 'Wait a second.' He darted from view and then reappeared, tossing holy water over him. Dean spluttered and spat water from his mouth, but Sam seemed satisfied with the result. 'Sorry. Dad told me to do that to strangers.'

_John Winchester - the reason for lack of social skills. _Dean mused, stepping into the room. 'Your dad is right. But I'm not a stranger.' He turned to face the boy, who still held the pistol at him, but not as firmly. 'You can put the gun down. I'm not a threat to you.'

The boy watched him for a long moment, then relaxed the pistol. 'No. You would have killed me in that playground if you were.' He put the gun down on the side. 'Why did you need to see me?'

'Just...did.' Dean finished lamely. He took a seat at the table, looking over the books. 'History huh?'

'Yeah, I got a school report to do.' Sam walked over to the table and retook the seat he'd been in before Dean showed up. 'So what's your name?'

'Huh?' Dean blinked, unsure of how to answer.

'You know, your name?' Nice to know Sam at bitchface at that age. 'I'm Sam and you're...'

'Dave. Hasselhoff.'

Sam giggled. 'No really. That's one my brother uses as an alias. Usually when he's chasing pretty girls.'

'Your brother sounds like a cool guy.'

'He's the best.' Sam smiled widely, then eyed him curiously. 'But who are you? Really? Like, no fake names.'

Dean held his breath for a second. Usually he could come up with a lie on the spot, but looking into Sammy's big puppy dog eyes, being back here, being with his _brother_ again, no matter what age he was, he was suddenly done with lying to him. He'd lied to him too much, and now he couldn't do it anymore.

'I'm Dean, Sam. I'm Dean from twenty ten.'

The littlest Winchester gaped for a moment, then smiled. 'No way! I _knew_ you looked familiar! Time travel is real?' He seemed more excited than shocked, but then Dean guessed, by this age, neither of them had been shocked by much any more.

'Sort of.' He said, smiling down at his younger brother.

'So why have you come back here? Why to see me?'

'Doesn't matter. Just did.' Dean didn't know if that excuse would fly but he tried it anyway. Sammy shrugged, still smiling.

'So what am I like in the future?' The boy asked and Dean smiled broadly.

'A little geekier and taller than you are now.' He replied, leaning forward.

'Do I have a girlfriend? Do I get to go to law school?' Sam's face dropped a little. 'I'm not a hunter am I? Like Dad? Cos I don't wanna be a hunter.' Dean felt something inside him twist up and die. He couldn't tell Sam anything. He didn't want to destroy his dream prematurely. Despite the fact that a lot of pain and anger faced him in the future, he couldn't tell Sam a thing about his future.

'I can't tell you any of that.' He said with a sad smile. 'But I can tell you that you grew up to be the awesomest little brother ever.'

* * *

It was three month later when Dean was in that field again, begging for Cas to show his face. This time the angel appeared after a few calls, looking a little too expectant.

'I was expecting you to call sooner.' He admitted when Dean pulled him on it.

'I was too.' The last Winchester replied. 'I held out for as long as I could, then Lisa had this dinner party and the whole time I wanted to tell Sammy something funny that had happened, or something Ben had done and...he wasn't there.' No emotion showed on the angel's face. 'I know I still can't tell him those things. Just...please Cas?'

'Okay, Dean.'

He knew where he wanted to go this time. When Sam was twelve he'd won a trophy for a debate team at high school. But when he returned home, triumphant, neither Dean or John had been there - they'd been hunting a poltergeist in the neighbouring town. So Sam had celebrated on his own. Dean never knew what he'd done that evening on his own, and he wanted to find out.

It was another crummy motel greeting him when he opened his eyes this time, and in that second he realised the truly crappy life they'd had all those years. He'd longed for a home and a family, and whilst he had the family mostly, even now, having the home wasn't enough. Because home wasn't home without Sam. And he was gonna have to live with that.

'Dean?' A small voice asked, and he turned, smiling at Sam. The boy was walking across the parking lot with his school bag. 'That you?'

'Yeah, it's me, Sammy.' Dean smiled, reaching out to ruffle the kid's hair. He wondered when Sam had shot up to his grown up height. He was impossibly tall.

'It's been two years, Dean. I thought you'd come back by now.' His voice was a lot more dejected than last time he'd seen him, and the light in his eyes a little more dimmed.

'Let's go inside, huh? I think someone's got some celebrating to do.'

'I don't feel like it.' Sam said, but led the way to the motel room anyway. 'Dad and Dean aren't here, and Dean said they would be.' He unlocked the room and opened the door, holding it for Dean.

'I know I did, kiddo, but you know what Dad is like.' Dean shut the door. 'I'd have given anything to be here. I guess, in a way, I have.' He muttered, looking around the motel room. Generic wallpapers, dodgy stains - yup, this was his childhood. 'You won something right? A debate at school?'

'Yeah.' Sam blinked. 'How - you're from the future. Right.'

'Right.' Dean looked in the fridge, contemplating a beer, but realised the blame would get pinned on Sam and he didn't really wanna do that. 'Look, I know for a fact that Dad and...me...won't be back for another few hours. So how's about we go get some dinner and celebrate your trophy?'

Sam contemplated it for a moment. 'Okay. But one thing first.'

Dean nodded, sitting at a chair in the kitchen. 'Anything.'

'This is the third time you've time travelled to visit me, Dean.' Sam's question was implied. _Why are you coming back here? Why do you wanna see me so bad?_

The elder Winchester plastered on an almost fake smile, looking at his little brother with what he hoped with sincerity. 'What's wrong with checking in on my little brother?' He slapped his hands on his knees. 'Now, go change your shirt. Dinner's on me.'

* * *

When Christmas came around, Dean felt a hole in his chest. Ben and Lisa were excited and there were parties galore, presents and endless family visits. Lisa's mom didn't approve of him, but Dean could care less. In fact, he did care less. And less. And even less these days. He went through the rigmarole with a lack of enthusiasm. He didn't want this life that he'd promised Sammy he'd lead.

Problem was he'd promised Sam he would live it.

It was the New Year before he could get away again. This time Castiel didn't even speak to him, simply sending him where he needed to go.

Dean leant against the wall, watching himself and Sam argue about Dean turning up at his apartment in the middle of the night, breaking in, and dropping the bombshell that Dad was missing. This was it. The moment he'd ruined his little brother's life. _Again._ This was when he'd been dragged right back in, right into the thick of it. This was what led to his imprisonment in the pit.

Sam walked away, heading back to his apartment, seething a little from Dean's dismissal of his interview. He walked into the alleyway that led to the staircase for the apartment, and Dean decided now was as good a time as ever. The younger Winchester paused, rolling his eyes.

'Dean, I just talked to you like a minute ago.'

'Don't listen to him. I was always proud of your interview.' Dean said, and the ball dropped with his brother.

'Dean?' He asked quietly, and the elder nodded. Unexpectedly, Sam rushed forward, throwing his arms around the future version of his brother. 'God, it's been ten years! I thought I was dreaming you.'

'No. No, man. I just...' He shrugged. 'I dunno.'

Sam pulled back. 'You okay?'

Dean ran a hand down his face. 'I just...just wanted to tell you Sam. I am always gonna be proud of you, you know?' He smiled tightly, a hitched breath in his throat. 'You're so smart and capable. Way better than me at the school stuff. And Jess? Hell, man, she's gorgeous.' _God, I wish I could tell him. Don't come hunt with me, Sammy. Stay home with your beautiful girlfriend. Stay in your normal life. Don't come with me. Stay.__ So I know you'll live._ But it wouldn't change anything.

Sam smiled, bashfully. 'You're way nicer than my Dean. He said she was out of my league.'

'I was a dick. No one is out of your league, Sammy.'

'You're not staying are you?' Sam said slowly.

'I can't.' Even now, he felt Castiel in the back of his skull, almost a hum reminding him that he couldn't stay, however much he wanted to. Dean smiled again. 'Just don't forget that I'm proud of you, Sam. Don't forget.'

* * *

'Dean. You cannot keep doing this yourself.'

Castiel was right of course. He couldn't keep doing this. It was killing him. Seeing Sam for brief moments, going back to his regular life with Lisa and Ben, knowing that he could stay, could change everything, except he couldn't...he was going crazy. It had been almost a year since Sam had died and left him to live this stupid apple pie life that he didn't want. And every now and then, he could escape, drive the Impala, see a past echo of his brother.

He couldn't keep doing it.

It was one or the other.

And he had to choose for Sammy.

'This is the last time.' He said quietly to the angel, who frowned at him, but complied nonetheless.

The motel door in front of him didn't look familiar. It was a plain door, white with a gold six on the front, and Dean raised a hand to knock tentatively. A few moments later and Sam opened it, looking at him in shock.

'Dean?' He blinked, the colour draining from his face. 'Dean, you're alive?'

He hadn't gone back so far. He'd been dead now. Buried in the ground for four months until Castiel pulled him out. And Sam was getting hooked on demon blood. _Add that to my list of reasons why I should have made him stay in Stanford._

'You're not my Dean.' Sam said quietly, stepping back. Dean walked into the room, looking around at the cartons of take out and weapons laying haphazardly on the table. 'You're future Dean.'

'Yeah.' Dean said quietly, wondering why he was torturing himself like this. In a few days Sam would have his real brother back. And then next year, Sam would give himself over to the Devil and Dean would be alone. Forever.

'This is good though. Because it means you're gonna come back.'

'You can't tell anyone you knew.' Dean said. 'Especially not me.'

'I kinda knew anyway, dude. First time you told me you were from the future, you came from twenty ten. Considering that's like, after now, when you're dead.' Sam's face fell a little. 'You died, Dean. I didn't...'

'I don't wanna talk about that.' The elder brother said slowly. 'I just...I wanted to say goodbye. And sorry.'

'Sorry for what? Wait, goodbye?' Sam looked panicked. 'Dean, I don't -'

'I'm sorry. I'm sorry I couldn't tell you about Jessica. That you didn't get the normal life you wanted. I'm sorry about everything that has happened and what is going to happen.' A warning tingle in the back of his head, Castiel telling him he was getting too close to spilling everything. 'And I...This will be my last trip.'

Sam's face scrunched up. 'Dean, you...you can't...none of it was your fault. The yellow eyed demon...Dad...none of it.' Tears were gathering in his eyes now. Dean squeezed his eyes shut for a second.

'I should never have let you leave Stanford.' He admitted. 'None of this would have happened.'

'Dean, tell me, what's going to happen?' Sam tried to coax it out of him, and the warning buzz became a stab in his head, causing him to wince. 'Dean, please.'

The eldest Winchester smiled at his brother, and approached him, hugging him closely. 'I love you, Sam. And I'll always be proud of you.' He pulled away and headed for the door, knowing he couldn't handle this. He had to go before he broke. As he reached the door and turned the handle, he looked back at his brother, memorising him, holding him there as he was - alive.

'I'll see you around, Sammy.'

* * *

The sun was filtering in through the windows as Dean laid in the queen sized bed. The smell of Lisa's fabric conditioner surrounded him, her perfume leaving a lingering smell on the pillow. He ran his hand over his forehead, feeling sick to his stomach. The house was empty and he was alone for the day.

It had been a year. A year since Sam had fallen into the pit. A year of Dean doing nothing but what his brother had wanted for him. He had a family, a house, the normal car, the normal job.

But he'd never have a home.

* * *

**Yup. Just broke myself. Sorry. Please let me know what you think. **


End file.
